We propose a method for the synthesis of diaryl-substituted pyridylmonoazatriphenylenes by the heterocyclization reaction of dihalosubstituted phenanthrenequinones with pyridine-2-carboxylic acid amidrazone, followed by aza-Diels–Alder reaction and Suzuki cross coupling. The obtained compounds showed more promising photophysical properties, compared to non-arylated analogs.
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B. H. Bakker, M. Goes, N. Hoebe, H. J. van Ramesdonk, J. W. Verhoeven, M. H. V. Werts, and J. W. Hofstraat, Coord. Chem. Rev., 208, 3 (2000).
T. R. Govindachari, N. Viswanathan, J. Radhakrishnan, R. Charubala, N. Nityanandra Rao, and B. R. Pai, Indian J. Chem., 11, 1215 (1973).
T. R. Govindachari, B. R. Pai, and K. Nagarajan, J. Chem. Soc., 2801 (1954).
C. W. Lim, O. Tissot, A. Mattison, M. W. Hooper, J. M. Brown, A. R. Cowley, D. I. Hulmes, and A. J. Blacker, Org. Process Res. Dev., 7, 379 (2003).
B. A. Sweetman, H. Muller-Bunz, and P. J. Guiry, Tetrahedron Lett., 46, 4643 (2005).
D. S. Kopchuk, I. N. Egorov, T. A. Tseitler, A. F. Khasanov, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 538 (2013). [Chem. Heterocycl. Compd., 49, 503 (2013).]
V. N. Kozhevnikov, O. V. Shabunina, D. S. Kopchuk, M. M. Ustinova, B. Koenig, and D. N. Kozhevnikov, Tetrahedron, 64, 8963 (2008).
A. H. Younes, L. Zhang, R. J. Clark, and L. Zhu, J. Org. Chem., 74, 8761 (2009).
H. S. Joshi, R. Jamshidi, and Y. Tor, Angew. Chem., Int. Ed., 38, 2722 (1999).
J. C. Loren and J. S. Siegel, Angew. Chem., Int. Ed., 40, 754 (2001).
G. Albano, V. Balzani, E. C. Constable, M. Maestri, and D. R. Smith, Inorg. Chim. Acta, 277, 225 (1998).
W. Goodall and J. A. G. Williams, Chem. Commun., 2514 (2001).
F. Hershnann, Ber. Dtsch. Chem. Ges., 41, 1998 (1908).
M. Krueger and E. Mosettig, J. Org. Chem., 5, 313 (1940).
N. P. Buu-Hoi, J. Org. Chem., 19, 721 (1954).
W. Marckwald, Justus Liebigs Ann. Chem., 274, 331 (1893).
P. J. Campos, E. Anon, M. C. Malo, and M. A. Rodriguez, Tetrahedron, 54, 14113 (1998).
O. Bilgic and D. W. Young, J. Chem. Soc., Perkin Trans. 1, 1233 (1980).
D. N. Nicolaides, K. E. Litinas, G. K. Papageorgiou, and J. Stephanidou-Stephanatou, J. Heterocycl. Chem., 28, 139 (1991).
I. Nagao, M. Shimizu, and T. Hiyama, Angew. Chem., Int. Ed., 48, 7573 (2009).
A. McIver, D. D. Young, and A. Deiters, Chem. Commun., 4750 (2008).
G. R. Pabst, O. C. Pfüller, and J. Sauer, Tetrahedron, 55, 8045 (1999).
A. Rykowski, D. Branowska, and J. Kielak, Tetrahedron Lett., 41, 3657 (2000).
D. S. Kopchuk, A. F. Khasanov, I. S. Kovalev, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin, Mendeleev Commun., 23, 209 (2013).
E. C. Taylor, J. E. Macor, and J. L. Pont, Tetrahedron, 43, 5145 (1987).
D. S. Kopchuk, G. V. Zyryanov, I. S. Kovalev, A. F. Khasanov, A. S. Medvedevskikh, V. L. Rusinov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 535 (2013). [Chem. Heterocycl. Compd., 49, 500 (2013).]
E. K. Unver, S. Tarkuc, C. Tanyeli, L. Toppare, and Y. A. Udum, J. Polym. Sci., Part A: Polym. Chem., 48, 1714 (2010).
F. Dewhurst and P. K. J. Shah, J. Chem. Soc. C, 1503 (1969).
P. Luliński and L. Skulski, Bull. Chem. Soc. Jpn., 72, 115 (1999).
D. Chaudhuri, K. J. van Schooten, S. Liu, J. M. Lupton, H. Wettach, E. Sigmund, and S. Höger, Angew. Chem., Int. Ed., 49, 7714 (2010).
K. Brunner, A. van Dijken, H. Börner, J. J. A. M. Bastiaansen, N. M. M. Kiggen, and B. M. W. Langeveld, J. Am. Chem. Soc., 126, 6035 (2004).
S. C. De, Q. J. Indian Chem. Soc., 4, 183 (1927).
J. Schmidt and H. Bürkert, Ber. Dtsch. Chem. Ges., 1356 (1927).
S. C. De, J. Indian Chem. Soc., 7, 361 (1930).
F. H. Case, J. Org. Chem., 30, 931 (1965).
V. N. Kozhevnikov, M. M. Ustinova, P. A. Slepukhin, A. Santoro, D. W. Bruce, and D. N. Kozhevnikov, Tetrahedron Lett., 49, 4096 (2008).
D. S. Kopchuk, A. F. Khasanov, I. S. Kovalev, G. A. Kim, I. L. Nikonov, G. V. Zyryanov, V. L. Rusinov, and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 936 (2014). [Chem. Heterocycl. Compd., 50, 864 (2014).]
S. Parker, Photoluminescence of Solutions [Russian translation], Mir, Moscow (1972), p. 251.
The work was performed with support from the Ministry of Education and Science of the Russian Federation (state contract 8430), Grants Council of the President of Russian Federation (grant MK 1511.2013.3), as well as the Program 211 of the Government of the Russian Federation (contract No. 02.А03.21.0006).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 943-952, June, 2014.
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Kopchuk, D.S., Khasanov, A.F., Kovalev, I.S. et al. The Extension of Conjugated System in Pyridyl-Substituted Monoazatriphenylenes for the Tuning of Photophysical Properties. Chem Heterocycl Comp 50, 871–879 (2014). https://doi.org/10.1007/s10593-014-1541-0
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DOI: https://doi.org/10.1007/s10593-014-1541-0